6 Answers
6

I ran D&D games on IRC for several years. The biggest challenges were:

Agreeing on a game time is tricky. When you've got international players, this is a major factor. We used a Google Calendar to post availability, and picked times when five or more were available.

Communication is more cumbersome online. It may not seem like it, but response time is slower in text. You have to finish typing before someone can start reading it, and after that there's a similar delay before you can reply. Combat moves more slowly, so people get distracted and miss their turn, which slows combat even more. The lack of body language in text is huge; you can't grab someone's attention or avoid interrupting someone.

You need to simulate dice. There are IRC dicebots and websites like dicelog.com, but not all instant messenger services have dice simulators available. You can let your players roll real dice, but it's extremely tempting for players to occasionally cheat and ignore a bad roll. If you need to simulate miniatures too, you'll need tools for that: Google Hangouts will soon have Tabletop Forge.

Some players won't take the game seriously. When you have to be at a physical location to play an RPG, you make a face-to-face commitment to show up. When it's online, it's easy to volunteer and then flake out. I regularly recruit six or seven players, expecting that one won't make it to the first session and another will drop out in the first month.

Text lacks human contact. There's a camaraderie in a regular in-person gaming group that you don't necessarily get in text. Even video chat is awkward, due to time delays. The in-person aspect isn't essential, but a lot of players miss it, and there's no real way to replace it with technology.

#2 can be a huge issue in drawn out combat. Players may alt-tab into browser windows when it's not their turn and become increasingly distracted. I've resorted to the rule that if I call a players name twice, I simply put them on auto-pilot and take a simple action for them.
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MadMAxJrSep 24 '12 at 20:20

This is an excellent post and all of these are real issues. That said, don't let it get you down! Online play has its issues, but it can also work well as long as you're prepared for them.
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KRyanOct 11 '12 at 16:30

I've played in numerous text-based games and the problems I encountered in those inspired me to work on my own text based gaming medium. While this answer will sum up problems I've encountered as Jonathan already mentioned some, it's also an ad for my free, non-profit text based roleplaying platform.

But first, issues I've encountered:
(IRC related)

Limited nicknames, changing not always desirable

Ping timeouts

Late arrivals need to be explained what they missed

Dice rolling usually requires a dice bot

Unable to know if someone is typing

No editing

Skype has these issues partially covered, but it still lacks in some areas;

No dice rolling by default, though I've previously programmed such feature through SkypeAPI

Can have sometimes annoying connection issues, such as messages not being delivered to every recipient

It's still a very minimalist overall experience, poor.. atmosphere?

No highlights

Ropeclient is my answer to the issues like above. It's easy to learn (but lacks decent documentation..), requires only a modern web browser to run, and can be used to play both real time and play by post style games (though now the focus is on real time only). I've run some gaming sessions on it, and the players generally enjoyed using it.

BUT I have yet been able to find another GM who would be willing to give it a try. Most (chat based) gamemasters stick to their preferred software and are not very open for alternatives. OK, I've only advertised the project a couple of times online, so that might also be just bad luck. And frankly speaking, because nobody is currently using it, I don't feel very motivated to spend time developing it.

I'm personally willing to guide anyone interested in trying ropeclient to learn the basics. It's easy - shouldn't take more than 10-15 minutes. I gladly take every possible feedback into consideration, be it positive or negative. You can get in touch with me for example through the ropeclient google group, Skype (same username), or.. gmail (still same username..).

Normally this kind of self-promotion is... questionable on this site: while it's definitely OK to mention your own work where it's relevant, it's important that doing so is not the only reason you have an account. Since this sounds pretty cool, I'm upvoting it, but I'd recommend becoming a part of the community and asking/answering some questions unrelated to this before you bring it up again, if only to show you're not just a promoter.
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KRyanOct 11 '12 at 16:37

FYI, "thread necromancy" is actually encouraged here, because the questions & their answers are neither threads (we're not a discussion site) nor are they ever considered "dead" (otherwise they'd have been closed long ago). So no apology for lateness is required! I edited it out for you, in fact. :)
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SevenSidedDie♦Oct 11 '12 at 19:54

Thanks! SE has answered many of my questions over the years, and I should have registered a long time ago. I'll be sure to contribute back to the community now that I took this one small step of registering..!
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snaipperiOct 11 '12 at 21:32

It appears that the link to Ropeclient is dead.
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Iron HeartJun 17 '14 at 3:17

We much preferred VSee to other chat programs and play-by-post or -e-mail gaming. As far as dice goes, you can't go wrong with dicelog.

The most difficult challenges was keeping people focused, from a DM perspective. Being at the same table contributes a lot. I combated this by preparing many, many speeches and such in advance, as well as working toward roleplay immersion as best as I could.

Also, finding a program to use maps easily with. Using VSee, I turned Excel/Calc into an easy dungeon model for combat. If you can, use RP Tools Maptools, I've heard it works beautifully but I haven't had the time, energy or patience to sit down and learn the system (it appears to be labor intensive as far as setup goes). Should that go well for you, please share your experience with those less smiled upon by the programming gods.

The best aspect was the time constraint lift as simply arranging a time to be online was enough, as opposed to waiting for people to arrive and allotting time for people to depart. That, and not having to hide all my papers behind a screen. Me being in front of the computer (where my backup PDFs are as well as the d20SRD) was more than acceptable, it was required.

The last part having been said, one of the worst aspects is your roleplaying is only as wide as your webcam/microphone can view/hear, and the fact that we human mortals are not designed to be in front of a desktop for incredibly long times with no reprieve. Walking away means walking away from your players, so recess is a lot less fun than when everyone's in the same room as I see it (I work extra hard on prep so I get recess as well when with the tabletop group).

Plenty of my sessions have gone long enough, as DM I could call it at six hours. I had the advantage of dedicated gamers, however - they had a lot of time slotted. The rest is all up to one's PC and internet connection, as well as those of everyone involved.

I played in an IRC game back in college. I don't remember how long the sessions lasted, but the game fizzled after a month or two.

Pros

The GM was able to copy and paste description. I think his doing this was what kept the game going at a good pace.

IRC dice rolling was easy. /roll 2d10. Trivial.

Infinite handles. What I mean by this was that if the GM wanted to introduce an NPC, that NPC had his own name in the channel. NPCs could talk to each other and it looked more natural than the GM talking to himself. At one point I lost track of who was an NPC and who was a PC, which was fantastic for my immersion.

Secret messages were secret. If the GM wanted to tell me that only I noticed the smell of gunpowder, the other players never saw the note get passed to me.

Cons

Player buy-in. The players just weren't that invested in a game full of internet strangers. I was the most reliable, but still forgot to show up to a session or two when a better option presented itself (although part of that is the GM's fault for doing a friday night game). TBH I wouldn't play a game with internet strangers again. I would do IRC with real life friends though, since I trust them not to ditch.

Typing speed. The GM kept up as best he could and the players interacted with each other where possible, but there was definitely time spent waiting. In tabletop if the GM does one on one chat with a player, it's transparent to everyone else. Here, it just looked like the GM ignored you.

Combat. I wouldn't want to play a high mechanics combat game in IRC. It just wouldn't be fun. We were doing WoD here, so I think it would have worked out had we played long enough to pick fights. But I wouldn't do a dungeon crawl like this.

Instead of interacting with people we were interacting with the internet. That needs clarification. How I react to the internet is different than how I react in real life. My character was a wealthy jerk who didn't want anything to do with the other players. Instead of taking offense at this, they all saw my character as that surly uncle and clung to him just because he was funny (see Bender in Futurama's Cyber House Rules episode). It was fun, but I didn't feel like I actually got to play my character because the internet PCs thought being a jerk was funny.

We had our first session last night and it was a tremendous success. We used Skype for both in-character text chat and out-of-character rules and clarifying discussion. I really like this because the result is a relatively clean transcript of the actual in-character bits and speedier resolution of the mechanical elements of game play.

Best of all, minutes before we were going to start, i found the amazing web service, Rolz, with its easy-to-use syntax, macro-ing, and best of all, Rolz Dice Room.

Awesome! If Skype chat (for IC) + Skype video (for OOC) + Rolz is the best solution for you, do mark your own answer as "Accepted" after the two-day waiting period. That's just so future RPG.SE users know at a glance that this question has been solved. Thanks! :)
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SevenSidedDie♦Sep 24 '12 at 18:38

You have to have a rules of order so that people aren't typing over each other and causing there to be multiple conversations going on at the same time in a shared chatbox. It can be an issue, but having some way for people to buzz in (such as a smiley emoticon as the signal they want to talk) can help keep order.

As for services, let me recommend roll20.net as a way to host your game. It's free, has built-in chat with dice rolling built right in. You can create macro buttons that will do the rolls without having to type it in every time, and the interface is really supportive for grid combat – it allows importing of images, objects, and sound files for use in your campaign.